In this study, we report the synthesis, antibacterial and anticancer evaluation of 38 novel phenanthridines that were designed as analogs benzo[c]phenanthridine alkaloids. The prepared differ from benzo[c]phenanthridines in absence a benzene A-ring. All compounds 6-bromo-2-hydroxy-3-methoxybenzaldehyde several synthetic steps through reduction Schiff bases accomplished by radical cyclization. Twelve derivatives showed high activity against Bacillussubtilis, Micrococcusluteus and/or...

Four new 3-hydroxy-quinolinone derivatives with promising anticancer activity could be solubilized using liposomes as vehicle to an extent that allows their in vitro and vivo testing without use of toxic solvent(s). A screening method identify the maximum incorporation capacity hydrophobic drugs within was successfully applied. The compounds lipid(s) were dissolved methanol, solvent removed by rotary evaporation. film resuspended phosphate buffer (pH 7.4), dispersion sonicated reduce vesicle...

Summary Cytokinins ( CK s) are pivotal plant hormones that have crucial roles in growth and development. However, their isolation quantification usually challenging because of extremely low levels tissues (pmol g −1 fresh weight). We developed a simple microscale magnetic immunoaffinity‐based method for selective one‐step s from very small amounts tissue (less than 0.1 mg The capacity the immunosorbent effect complex matrix on yield rapid purification were tested using wide range...

6-Chloropurine and 2,6-dichloropurine were regioselectively glycosylated at position 7 to give the corresponding peracetylated N7-nucleosides, which can be suitable for other purine transformations. In this work, we study distribution of N7/N9-isomers produced via Vorbrüggen method under different conditions, using an N-trimethylsilylated derivative SnCl4 or TiCl4 as a catalyst. The main effort is devoted reversing disadvantageous predominant selectivity most glycosylation reactions N9 thus...

Abstract N , ‐dialkylaminoethane‐2‐thiols belong to the group of precursors and degradation products chemical warfare agents (CWAs). These compounds were analyzed by means electrospray ionization‐multiple stage mass spectrometry (ion trap) proposed fragments confirmed accurate measurement using a QqTOF system. The fragmentation pathways studied oxidation (formation ‐S‐S‐ linkage) described. Some minor interesting processes, such as rearrangement SH group, observed proved. A new µLC/MS...

Abstract This study describes the oxidation of sanguinarine (SG) and its metabolite dihydrosanguinarine (DHSG) on surface a basal‐plane pyrolytic graphite electrode (PGE). Since both alkaloids strongly adsorb onto graphite, measurements were performed using ex situ voltammetric methods, adsorptive transfer (AdT) cyclic voltammetry (CV) square‐wave (SWV). Oxidation peaks SG (peak A) DHSG A*) observed around potential +0.7 V (vs. Ag/AgCl/3 M KCl), depending experimental conditions. The A A*...

The cyclization of 3-bromo-6-methoxy-2-(naphtho[2,3d][1,3]dioxol-5-ylaminomethyl)phenol (2) using tributyltinhydride under radical-mediated conditions was accompanied by spontaneous oxidation and 4) isolated as a side product.Isodecarine also prepared the catalytic debenzylation 7-benzyloxy-8-methoxy-2,3-methylendioxybenzo-[c]phenanthridine (5).This compound efficiently converted to 7benzyloxy-8-methoxy-5-methyl-2,3-methylenedioxybenzo[c]phenanthridinium trifluoromethanesulfonate (6) in high...

Abstract The first nitration of codeine by using bismuth nitrate pentahydrate under mild reaction conditions is described. resulting 1‐nitrocodeine was reduced to 1‐aminocodeine, a key precursor for the synthesis azo derivative and several hydrazones. Structures both 1‐aminocodeine were unequivocally determined single‐crystal X‐ray analysis. reported preliminary synthetic study lays groundwork modified derivatives with potential biological activity.

Abstract A method based on the coupling of capillary electrophoresis with mass spectrometry (CE/MS) was developed for monitoring 3‐quinuclidinol and its four N ‐alkyl derivatives (methyl, ethyl, propyl isopropyl derivatives). fragmentation study (collision‐induced dissociation ions in an ion trap) optimization optics set‐up CE/MS experiments using direct infusion a methanolic solution standards into spectrometer were carried out advance. Molecular all quaternary compounds quasi‐molecular [M...

The synthesis of some 2-(dialkylamino)ethanethiols is described.A method involving formation isothiouronium salts from 2-(dialkylamino)ethyl chlorides by the reaction with thiourea followed alkaline hydrolysis has been chosen.Prepared compounds can be used as standards for analytical chemical methods to monitor warfare agents and their precursors or metabolites.

Abstract Selected precursors and degradation products of chemical warfare agents namely N , ‐dialkylaminoethane‐2‐ols, ‐dialkylaminoethyl‐2‐chlorides some related ‐quaternary salts were studied by means electrospray ionization‐multiple tandem mass spectrometry (ESI‐MS n ). Proposed structures confirmed with accurate measurement. General fragmentation patterns these compounds are discussed in detail suggested processes using deuterated standards. The typical elimination alkene, hydrogen...

The corresponding 2-arylhydrazones 5 were obtained by coupling of diazonium salts with diethyl (3-methyl-1H-pyrrole)-2,4-dicarbamate 4.These ones cyclized in a alkaline medium to ethyl (2-aryl-5-methyl-3oxo-2,3-dihydro-7H-pyrrolo[3,2-e][1,2,4]triazin-6-yl)carbamates 6 and tested for their stability.The starting carbamate 4 was prepared multistep synthesis from 3-methyl-1H-pyrrole-2,4-dicarboxylate 1.

A simple general synthesis of 1-aryl-6-azaisocytosine-5-carbonitriles 4 is described. This method based on coupling diazonium salts with cyanoacetylcyanamide 2 and then cyclization the formed 2-arylhydrazono-2-cyanoacetylcyanamides 3. The 6-azaisocytosines were studied respect to tautomeric equilibrium transformation functional groups, used in condensed heterocyclic compounds: Purine isosteric imidazo[2,1-c]-[1,2,4]triazine 8 1,2,4-triazino[2,3-a]quinazolines 9-12.

Synthesis of [ 15 N 4 ] purine labeled cytokinine glycosides derived from zeatins and topolins containing a 9‐β‐ d , 7‐β‐ ‐glucopyranosyl, or ‐ribofuranosyl group is described. These 6 ‐substituted adenine derivatives are intended as internal analytic standards for phytohormone analysis. All compounds were prepared 6‐chloro[ ]purine ( 1 ). The equilibrium reaction with acetobromo‐α‐ ‐glucose gave isomeric 3 ) chloro glucosyl precursors, which treated the corresponding amines to get desired...

Abstract A series of 6‐azacytosines 4a‐4k and 5a‐5c were prepared by nucleophilic cleavage furan ring [1]benzofuro[2,3‐ e ][1,2,4]triazine derivative 1 . Some them used for the preparation derivatives [1,2,4]triazolo[4,3‐ d ( 6a‐6d ) tetrazolo[1,5‐ (7). The reaction with hydrogen sulfide afforded corresponding 6‐(2‐hydroxyphenyl)‐2‐phenyl‐5‐thioxo‐4,5‐dihydro‐1,2,4‐tri‐azin‐3(2 H )‐one 8 ), while selenide 6‐(2‐hydroxyphenyl)‐2‐phenyl‐4,5‐dihydro‐1,2,4‐triazin‐3(2 9 was formed. compounds...

A new N7 direct regioselective method allowing the introduction of tert-alkyl groups into appropriate 6-substituted purine derivatives is developed. This based on a reaction N-trimethylsilylated purines with halide using SnCl4 as catalyst. In this work, we study structure and optimal conditions leading to isomer in some cases also N9 isomer. The main goal devoted preparing 7-(tert-butyl)-6-chloropurine suitable compound for other transformations. stability tert-butyl group at position tested...

A series of 5C and 5N substituted 3-oxo-2-phenyl-1,2,4-triazine-6-carbonitriles 8-imino-2-arylpyrimido[4,5e][1,2,4]triazine-3,6(2H,5H)-diones (6-aryl-6-azapteridines) are described via a cyclocondensation reaction from the corresponding aryliminohydrazones with CDI.The required were obtained starting compound -malononitrile.These prepared compounds tested for cytotoxic activity on cancer cell lines.

Abstract Deuterium‐labelled derivatives of 2‐(dialkylamino)ethanols, 2–(dialkylamino)ethyl chlorides and 2‐(dialkylamino)ethanethiols have been prepared in which completely deuterated N ‐alkyls (Me, Et, n‐Pr, iso‐Pr) introduced as substituents. Such labelled are great interest mass spectrometry standards for monitoring chemical warfare agents their precursors. Copyright © 2008 John Wiley & Sons, Ltd.